Why I Do Unsmart Things

I have this fundamental belief. 

And this belief often leads me to do unsmart things. 

The heart of this belief is that if something I’m doing is going to succeed, then I have to do every possible thing to make it so. Now, doing so doesn’t ensure success but ultimate success is predicated on it. Call it necessary, not sufficient.

For better, but occasionally for worse, this belief can drive some over the top behavior. Flights for in person meetings that could have been done by video conference or over the phone. Ultra early or excessively late meetings just to squeeze one more into an already packed day. Email or IM sessions that run on long after every sane person in my house has turned in for the night.

I was forced to think hard about this belief as I drove to catch my red eye flight last night.

Just the day prior I’d been in my doctor’s office, finally admitting I was sick, and picking up 4 different prescriptions to ward off this particularly nasty strain of slow death I was fighting. As I drove, and the cold sweats started kicking in, I was forced to think about why I was still planning to get on my flight.

Not only would I be putting my health at further risk, but I was putting the health of those on my flight and those in the board meeting I was planning to attend at risk. And for what? 

As I thought of the underlying motivations that were driving this behavior I started to realize that this wasn’t about the company’s board meeting. This wasn’t about doing every possible thing I could to ensure they succeed. This was about me. 

Ultimately, my motivation for getting on that red eye was a selfish one. Show the team that I’m committed to their success. Show my team at OATV that I was willing to go the extra mile for our founders. Show my family that I was committed to ensuring our future. This wasn’t about throwing my health, my calendar and my heavily medicated mental state on the alters of startup sacrifice, this was about how I looked to everybody else.

In light of this personal revelation, and as the cold sweat poured down my temples, I veered off course from SFO, headed home, crawled into bed and have been here ever since. 

As I lay here, I can’t help but wonder how many of the herculean sacrifices we make in startupland are rooted in my fundamental belief and how many of them are rooted in our own selfishness. I know so many founders and employees at startups who sacrifice so much of their personal lives, personal hygiene and personal health to ensure their company’s success. But who is it really for? 

Last night’s insight into my own motivations is one I want to pay more attention to going forward. It doesn’t mean I won’t do plenty more unsmart things. But I want to be more aware of the “why” behind the ones I do.